


Pretty

by perpetuallycaffeinated



Category: Supernatural
Genre: Crossdressing, Frottage, M/M, Panties
Language: English
Status: Completed
Published: 2012-05-23
Updated: 2012-05-23
Packaged: 2017-11-05 21:25:54
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,693
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/411180
Author URL: https://archiveofourown.org/users/perpetuallycaffeinated/pseuds/perpetuallycaffeinated
Summary: <blockquote class="userstuff">
              <p>Castiel finds out about Dean's secret about those pair of pink panties, and is...intrigued.</p>
            </blockquote>





	Pretty

Castiel tried to ignore it, he really did. Dean didn’t help things by thinking so loudly. He couldn’t always hear inside the hunter’s head. It only happened when he and Dean were side by side, with the hunter relaxed and combing through his memories. Even though it had only happened a handful of times, Castiel knew that Dean would “freak” if he found out. He would have informed Dean about the phenomenon, but...it was a moment of weakness, and Cas knew it. The thoughts, the memories that floated through Castiel’s mind were never scandalous. The angel only saw quiet nights sipping beer with Sam, rare moments when the three Winchester men were together and happy. Dean’s thoughts were echoes of calmer times. Castiel found himself hard-pressed not to catch a glimpse of his charge before he had felt the flames of Hell.

  


Leaning back in his chair, Castiel cast a sidelong glance in Dean’s direction. He was still sprawled across the motel bed, thumbing through a book. It was times like this between hunts and demons, when he could almost completely relax....yes. There it was. Castiel felt something prying at the edge of his awareness. Dean’s thoughts were always much more eager to share themselves with the angel than the man himself. Closing his eyes, Castiel allowed the thread of Dean’s stream.

  
Sammy wasn’t in this memory. Nor was John Winchester.   
  
Or very many clothes.   
  
Castiel opened one eye to make sure Dean’s state hadn’t changed. He wouldn’t put it above the hunter to send him inappropriate images on purpose if he’d discovered what Castiel was doing. However, Dean was still staring at his book, oblivious to the rest of the world. Whatever was entering his head, it was authentic. Closing his eyes again, Castiel concentrated on the images in his head. There was a younger Dean, perhaps in his late teens, with a woman roughly his age. From what Castiel knew of human mating, the two appeared to be at some stage of the process. Castiel felt Dean’s remembered embarrassment, mixed with confusion and a strange addition of arousal.   
  
Dean was wearing his partner’s underwear.   
  
Thanks to rampant advertisements across America, Castiel felt that he had a basic idea of what men and women were expected to wear under their clothing. Men had boxers, or what Dean derisively called “tightey-whiteys.” Women had...well, women had much, much more. Castiel returned to Dean’s memory, but the additional details only confused him even further. Why would Dean, who insisted on never having a “chick flick” moment, willingly put on clothing intended for a woman? He let the memory fall away and turned his attention back to the man on the bed. Though he understood the basics of “appropriate” gender division, the revelation stirred no disgust in him. Only slightly bewildered curiosity. After all, this wouldn’t be the first time that he found a pressing issue in human culture when there was none.   
  
“...pink?”   
  
Dean didn’t move a muscle. His eyes remained trained on the book, but he was no longer reading.   
  
“What did you say?” Dean was trying to sound calm, but his voice came out as a rough croak. Cas had seen him face down demons, but never with this terror in his voice. Only women’s underwear had the power to strike the fear of god into Dean Winchester.   
  
“I said ‘pink.’ Why were you wearing--”   
  
“Jesus, Cas! Don’t say it!” Dean hissed, sitting bolt upright on the bed. “And--how--stay out of my head!”   
  
“I did not enter your head,” Castiel countered, fixing him with an even stare. “It is not my fault you can’t keep your thoughts to yourself. Why did you wear pink underwear?”  
  
Angels were not big fans of an artful segue. Castiel was shifting gears without the clutch, and Dean’s brain was quickly locking up as he tried to decide just what to start yelling at the angel for. As he spluttered and cursed, Castiel waited patiently for an answer.   
  
After an brief, intense internal battle, Dean gave up. Sighing, he shifted over to the edge of the bed. Though he motioned for Castiel to sit beside him, he still stared at the wall, determined not to make eye contact.   
  
“Get over here, lock all the doors with that mojo, and listen close, because I am never, never going to repeat this.”   
  
The angel nodded, sitting down and leaning in until he was only a few inches away from Dean’s face. If this knowledge would only be revealed once, he was determined not to miss any nuances.   
  
“...Okay, you don’t have to listen that closely,” Dean grunted, sliding over to widen the distance. Taking a deep breath, he had to close his eyes before he could begin talking.   
  
“Look, sometimes, guys like to wear chick’s underwear.” Dean refused to physically say the word “panties.” “It’s not really something you’re supposed to do, so part of it can be...I dunno, something to do with that whole submissive, ‘you’ve been a bad boy’ thing.”   
  
Castiel nodded slowly, trying to process the new information. “Forbidden fruit,” he offered, an effort to try and quell Dean’s anger. The surprised, choked sound Dean made was not the reaction he had been fishing for.   
  
“Cas, do me a favor. Don’t ever say that again.”   
  
Dean stared Castiel down, only resuming his lecture once the angel gave another slow nod.   
  
“And, well, guys don’t get good underwear. Grey and white with shitty cotton is about it. The stuff that’s made for girls, with silk and crap...” Even though Castiel’s face remained completely neutral, Dean felt heat rising in his cheeks as he continued to speak. He screwed his eyes shut tighter and hoped Castiel wouldn’t clue into how uncomfortable he was. “Itjustfeelsreallygoodonyourjunkokay?” The words came out in a jumbled rush. When Dean dared to open his eyes again, Castiel was still steadily staring at him.   
  
“You going to look at me funny from now on?” He joked, trying to return the situation to an easy, shallower context.   
  
Just because Castiel knew Dean do his core, it didn’t mean the man did not utterly confound him at times.He had dragged him out of Hell away from a scene of torture and blood. How would something as small and utterly earthly as what cloth he wore change his opinion?   
  


“No, Dean. Though you already complain about how I look at you.”  

  


“Yeah.” Dean snorted. “I guess you can’t look at me even weirder than you usually do.” Pushing himself up and off of the bed, Dean wandered into the bathroom and shut the door behind him. He wasn’t hiding from Castiel. He was just moving somewhere where Cas was not. To his relief, the angel didn’t follow him into the bathroom. Dean balanced on the edge of the motel bathtub, cradling his face in his hands. Why did it still feel like Castiel was staring at him? 

  


“This is the last time you ever bring this up, you hear?” He hollered through the wall. 

  


Castiel was staring at the door. He knew Dean was inside, but could no longer see him. “Yes, Dean,” he answered, voice quiet. “This will be the last time. 

  
  
  
  
It was not the last time.   
Almost a month had passed since that awkward conversation. Castiel had held true to his promise of silence. Dean was almost proud of the development. His awkward nerd angel was slowly becoming slightly less awkward.   
  
Then Wal-Mart ruined everything.   
  
When Sam and Dean pulled into the mega-center to stock up on rock salt and accelerant, Castiel tagged along. Despite Sam’s objections , Dean had shoed a crumpled shopping list in the angel’s hands with orders to ‘start pulling his own weight.’ Castiel didn’t understand why Dean needed him to shoulder other responsibilities other than ‘angel of the lord devoted to following your orders.’ However, this was yet another one of said orders, he took the list without further complaint and shuffled off into the depths of Wal-Mart. If he could find Dean’s souls in the depths of Hell, he could find ‘new socks for Sammy--as big as possible.’   
  
Unfortunately for Dean, the super-center placed socks next to another article of clothing. Once Castiel had grabbed the largest looking socks in hopes that they would fit Sam, something else caught his eye. The store’s underwear section. He had promised Dean not to bring up the topic again, but he hadn’t agreed not to pursue the matter further on his own.   
  
The men’s underwear was nothing new to him. Even hunters had to do laundry, and Castiel had seen tattered boxers, black and grey fabric in a messy pile on motel room beds. Save for a few different shapes, there was nothing Wal-Mart had to pique his interest.   
  
Women’s underwear was a different matter all together. Where the men’s clothing was drab and neatly organized, the women’s underthings were jumbled together into an orgy of colors and soft fabrics.   
  
Castiel inched closer and placed one hand on the side of the display, fingers giving a betraying twitch of uncertainty. He was proving his weakness for earthly enjoyments once again. Angels were, in theory, allowed to enjoy things. Castiel was not reprimanded for finding joy in the beauty of their father’s creation, or for finding satisfaction in serving the will of the Host. However, the small pleasure offered by this pile of underthings carried a real threat. His superiors in Heaven had already censured him for indulging in emotional attachment. Even if things like this did not cause a soldier to fall, it could cloud his ability to follow orders faithfully and make it objective to maintain sight of his mission.   
  
He curled his fingers around the cheap particle board, steadying himself against the display case. It would be alright; he was a warrior of god. Man-made fabric would not threaten his allegiance to Heaven. After all, he had already allowed himself something far more dangerous: Dean Winchester.  
  
Somehow, the thought of the Hunter didn’t help him calm down. Nevertheless, Castiel forced his fingers to relax, and he slid one hand straight into the pile of underwear.   
  
Oh.   
  
Castiel opened himself up to all of the information his vessel’s nerve endings had to offer, and was rewarded by a flood of sensation. How was it possible for something as simple as cloth to have so many different textures? Silk and lace with delicate folds, weaves catching on the tiny ridges of his skin like a revelation from above.   
  
“Son of a bitch, Cas, what do you think you’re doing?!”  
  
The angel’s foray into Sins of the Textile was cut short by a firm hand yon the back of his coat. It was Castiel’s only other earthly indulgence. He let Dean drag him out of the aisle, out and around back to the safer realm of socks. Once they were safely hidden from any passing judgement of middle American soccer moms, Dean looked down at Castiel’s hands and cursed again. The angel had been cooperative, but his hand had not. Clutched in determined fingers was a pair of deep blue, lacy panties.   
  
“We are not buying those,” Dean hissed. Castiel didn’t look up, still staring at the object in his hands. Though he could feel Dean’s soul crackling behind his ribs, he tuned out his voice, rubbing the fabric of the underwear between his thumb and forefinger.   
  
“It’s soft.” Two murmured words, and Dean stilled.   
  
“I can’t believe this.” Dean’s voice remained low and strained, but he curled his hands around Castiels, bunching the panties up into a ball in the center of their joined fists. “You’re coat’s got an inside pocket, right? Just stick it in there and shut up about it.” When Castiel didn’t move, he cursed again, then pushed his way into the angel’s coat to hide it himself.   
  
“Frikkin great angel you are, flasher coat with chick’s underwear shoved in your pockets...”   
  
Castiel nodded quietly, his eyes still cast down at Dean’s hands as they fussed and adjusted the coat to conceal the shameful bundle. It was the best response when Dean began rambling. In this situation, it seemed like Dean did not want a response, anyway. The longer he stayed on the earthly plane, the more he noticed that humans spoke to themselves in times of distress. It struck Castiel as a desperately lonely gesture; how bad was it when the inside of one’s head was no longer enough comfort? His interest in the underwear was suddenly overshadowed by the urge to reach out to Dean.   
  
“Do you need socks?”Castiel asked, his face blank. Castel nodded, looking back to the underwear section where Sam’s package of socks lay lonely and forlorn.   
  
“Socks. You instructed me to find them for Sam, but not for yourself. Are you in need of socks?”  
  
Dean was still for a moment. Even for the angel, it seemed like a long stretch of time. Castiel felt as though he was being weighed in that moment, searched for some quality or fault that Dean suspected. To his shock, he found himself caring whether or not he passed this examination.   
  
Whatever Dean found, after a few more seconds, the tension in his shoulders eased.   
  
“Yeah, you can get me some socks,” Dean snorted, relying on derision to cut the tension that had slowly grown between the two men. “Just make sure they’re made for men.”   
  
  
  
After the incident in Wal-Mart, Castiel had kept his promise. Both brothers’ sock supplies were restored. As Dean asked, his socks remained firmly heterosexual. His dreams, however, did not.   
  
The first was three nights after their trip to the store. They had not found any seals or demons in the time; Dean figured his mind was too restless not to fuck with him. Instead of Hell, it opted for--  
  
Castiel spread out underneath him, wearing those stupid fucking blue panties. He was on top of the angel, not even bothering to take them off. Shoving them to one side so they stroked his shaft as he pumped in and out of that tight body--  
  
\--and waking up, chest heaving from a mix Gay Angel Panic and base arousal. Dean did what he always did; ignored the problem. And the dreams kept coming. The sight of Castiel holding those flimsy underpants must have wakened some latent pervert inside him, because every night brought Castiel, looking ridiculously hot, and always in those panties. Sometimes blowing Dean, sometimes letting Dean mouth at him through the fabric till it was wet and clinging, and other, gut-churningly wonderful times, letting Dean sink into him over and over till the Hunter woke up with an erection and pressing life questions.   
  
Whenever something bothered Dean (or even worse, threaten his manliness) he would invariably respond the same way: play stupid and ignore the troubling situation until it simply disappeared. However, this tactic wouldn’t work with Castiel. The angel wasn’t exactly his shadow, but now that Dean was haunted by the dreams, it seemed like he was always there. Castiel hadn’t alluded to the experience in Wal-Mart, but his very presence, those blue eyes and thick lips felt like accusations all in themselves. Even the angel’s fierce presence in battle somehow became sexually charged in Dean’s eyes.   
  
The Winchester managed to silently torture himself for almost two months before it all became just too much. The three men had been attracted to a small town in Oklahoma by the hint of demonic signs. Just when everything seemed to have been a false alarm, they had been ambushed by a small band of demons with dreams of proving themselves to the big daddy in the Pit. When one of them had gone after Sam, it had fallen like dominos. Sam was in danger, so Dean threw himself in. Which meant Dean was in danger, and so Castiel followed into the fray. The angel laid down a heavy smiting with a side of exorcism, but one of the demons had managed to set off a failed attacked before being burned out of its vessel’s body. Thankfully for all of them, it had done no actual harm.   
  
Unfortunately for Dean, it had managed to tear his vessel’s clothes to shreds.   
  
Once he was absolutely certain that Sam was in one piece, Dean turned his attention to Cas, and immediately regretted it. Castiel looked mildly annoyed at the loss of his coat, but either he hadn’t registered the damage to his pants, or he just didn’t care. But oh, Dean cared. The article of clothing was intact enough to remain clinging to his hips, but just barely. It hung on almost half-heartedly, slipping down Castiel’s slim vessel to reveal slivers of pale skin in ragged patches through the damage.   
  
Pale skin and blue. Blue. Fucking blue.   
  
As soon as Dean registered the color, he thought he’d gone insane. As soon as he registered lace, he was absolutely sure of it. This was something that belonged inside of his sick, twisted head, not reality. He completely tuned out the rest of the world, staring at the offending color while his mind flew off into a million different directions.   
  
“Cas,” he finally croaked out, grateful that Sam was too busy dragging the bodies into a pile to notice his brother had lost his goddamn mind over an angel in panties. “What...”  
  
Castiel looked down at himself, and yes, he was just realizing that more than just his skin was exposed. Then he looked back up and locked eyes with Dean, and everything slid into place.   
  
Cas was fucking amazing. He was a complete prick. He had a knack for treating Dean like a pissy child, had even threatened to hurl him back into Hell. He was amazing, strong and terrifying and panting hard from banishing evil with a touch of his hands. And. He was wearing. Panties. This terrifying creature creature wanted the same slick feel of fabric on his body, fabric Dean had given him. Dean didn’t even think he could feel the heat spread through his body. It was overwhelming and immediate, from on to off, mindless to burning in an instant.   
  
“We need to go outside. Right now.”   
  
Dean didn’t even wait for an answer. If Castiel was wearing them, some part of him was at least curious about the same thing Dean was. His suspicions were confirmed when he pushed himself up to his feet. It wasn’t graceful at all; the man staggering up and across the distance between himself and the angel, crashing into Castiel with heated momentum. Cas only got a chance to gasp in surprise before Dean was yanking him out and around to the abandoned lot behind the building.   
  
Dean wasn’t fooled for a damn second. He didn’t stop, whipping the angel around and out and down, throwing both of them down onto the bare dirt. He wasn’t good with talking about this, but he was in his element now, riding high on lust.   
  
“Don’t give me that surprised bullshit,” Dean rasped into Castiel’s ear. The angel just gave another sharp gasp in reply, eyes wide and wild as he struggled to make eye contact with the man on top of him. “You could be out of here in a second, or send me--” he swallowed, not wanting to mention the pit out loud even in this situation- “send me back, or send my flying, if you really didn’t want me on top of you.”   
  
Castiel still didn’t speak, but something flickered in his eyes, and Dean felt the slim body underneath him arch up against him. Sneaky fucker. Angels had great poker faces, but there was no way there was more going on underneath. Dean wasn’t the only one who danced around the facts of a situation when it didn’t suit him.   
  
Sliding his mouth up farther, Dean flicked his tongue out against Castiel’s chin, indulging himself in a brief taste of skin and salt before pressing his mouth against the other man’s. Now he wanted Castiel to talk. Knowing someone wanted it and getting to hear about it were two different things. “C’mon, Cas. Talk.”   
  
“Dean.” It’s a harsh gasp, only one word, but it seems to be the only thing Cas needed to say. Castiel’s mouth is smashed up against Dean’s so that the hunter’s name comes out half-mumbled and garbled, but even that ridiculous sound was the most beautiful thing Dean’s ever heard. He grunts encouragement before letting his body surge down, grinding up against Castiel as he finally pushes his way inside of the angel’s mouth.   
  
Even as Dean’s hands are pushing themselves down Castiel’s sides, he remained hyper-aware of two hands on his own body. He was spot on with his read of the angel. As passive as Cas had been in getting to this point, it wasn’t for lack of want. The moment Dean’s name had passed over his lips, it seemed the angel had let something loose inside of himself. As Dean ripped the remnants of those pants down, there were hands on his back, his shoulders, fisting in his hair only to flee once again to trace the line of his upper arms. The man found himself grinning--it was flattering, really.   
  
“Greedy, Cas,” Dean growled, teasing the angel even as he followed the slope of the angel’s neck with a swipe of of his tongue. Finally, finally, he managed to get his hands between their two bodies. Castiel wasn’t the only greedy one rutting in the dirt and weeds. he shivered in unmasked delight as his fingers brushed over the soft cloth that had started this all.   
  
As intended, his teasing got a rise from Castiel. He gave a soft grunt of annoyance, hands finally moving with purpose to slap Dean’s ass in warning before moving around to struggle with his belt. To his credit, it only took him the better part of a minute to give up learning how zippers and buttons work and simply rip the contraption open instead. Dean cursed at the sound of rending zipper teeth that close to his erection, but he escaped unscathed. He only got a second of relief before both of Castiel’s hands surged forward again, yanking his jeans and boxers down until they stopped awkwardly at his knees. The angel didn’t seem to mind how ridiculous both of them looked, and Dean was too horny to care.  
  
Castiel’s hands made no move to jack him off. They simply explored him, his achingly hard cock and hips with the same greedy joy as the rest of his body. Dean wasn’t complaining; with his own clothes gone, he was free to shamelessly grind down against the silky underwear. As good as the panties from his teenage years had felt, it paled in comparison to the flood of sensations he was currently being assaulted by. Slick fabric, damp in places where both of eager cocks had smeared precome, all just barely hiding Castiel’s arousal. Dean pushed one hand against the dirt and gravel beside Cas’ head, ignoring the sharp press of stone against his palms as he used the position for more leverage. There was no way the dreams would fade after this, no way that Dean’s mind could ever tire of a flushed, gasping angel writhing up against him as he pistoned their hips together over and over under the hot Oklahoma sun.   
  
As he fucked them together, Castiel’s hands had stilled, clinging for dear life to Dean’s back. The hunter was so absorbed in his task, he didn’t notice when those hands slipped, sliding down and between them to give one single, sharp tug to the panties still clinging to Castiel’s body. For one brief, horrible moment, Dean thought Castiel was taking them off, but then the fabric merely shifted to one side, his cock slipped, and then it was oh god inside. Dean tried to say something, anything, but all that came out of his mouth was a broken moan. His dick, slicked with the combination of sex and sweat, had easily slipped in under the hem of the leghole. Now Dean wasn’t just imaging the feel of Cas’ dick; it was right there, cock to cock in a mirror image of the two men themselves, sweaty and desperately rutting together.   
  
Every thrust now drew an extra whimper from Castiel, and when Dean finally realized why, he had to mentally will himself from coming. They were both trapped in the confines of the panties Castiel was wearing, and the article of clothing had been fairly well sized to match Castiel’s body. Now they were too tightly stretched, too much stuffed into the flimsy things, and each jerk of Dean’s cock was pulling the fabric up, putting pressure on Cas’ balls and ass. He managed not to come at the thought, but Dean couldn’t help the stream of filth he found pouring out of his mouth, growling into Castiel’s ear as a counterpoint to the angel’s breathless whines.   
  
“Fuck, Cas, ah fuck you like that? You like it with my cock on yours? I’ll bet you like it touching you back there too--” The words were a low rumble, that low gravelly octave of sex and lust from Dean’s chest. “I wish I could see how we look all tangled up in this stupid fucking underwear, but it feels fantastic. You wish it was me touching you back there?” he practically spat. Dean was close now, tension, frustration, lust all bundled together into a hysterical need. To his amazement, Castiel nodded frantically as he give another gasp. Dean thought he heard his name somewhere in the noise. Angling his thrusts, Dean reached down and grabbed both of them with one hand through the panties, feeling the extra tension cause the fabric to bunch and slide deeper between Cas’ cheeks. It must be the biggest tease, to have that soft fabric rubbing his hole, and Castiel’s noises weren’t proving him wrong.   
  
“Come on, come,” he urged, mouth still pressed urgent and messy up against the other man’s ear. “Come for me, Cas!” he growls, and whether it’s because it’s practically an order and the angel’s freakier than he thought, or because it’s the sound of his name on Dean Winchester’s lips, Castiel comes then, shaking under Dean as he spills the evidence of his first human pleasure out over both of them. The knowledge that he’s just made this creature orgasm is enough to send Dean over as well, and he fills the panties with his own semen, still half-gasping the angel’s name.   
  
They didn’t lie there for long. They simply didn’t have time to, with Sam still burning the bodies, but for once in his life, Dean broke the silence with an honest question.   
  
“Why...why were you wearing them?”  
  
He gestured down to the panties, now a wrinkled mess of jizz and sweat clinging to Castiel’s hips. Castiel kept his eyes closed, but he responded.   
  
“You gave them to me.”   
  
A simple sentence, but loaded with far more than a quick, adrenaline-fueled rubfuck behind a warehouse. Dean closed his eyes and let his head drop down to rest on Castiel’s shoulder. here it came, the building wave of guilt. He got a free pass out of Hell, and fucks an angel, who’s apparently frikkin’ sentimental over him. He opened his mouth to try and say the cruelest thing he can think of, to try and cut this off before it can twine around them any further, but Castiel beats him to the punch.   
  
“You have gravel in your hair.”  
  
His voice was low and tired (Dean takes a hint of pride in that), but there’s a lilt of something else to it. Dean raised his head just in time to see hooded eyes gaze up at him with something the Winchester refused to call anything but ‘extreme fondness,’ and a hand was coming up to card through his hair and dislodge the bits of gravel and sand that had somehow burrowed into the short locks.   
  
And Dean not only can’t think of a way to stop this. He doesn’t want to.   
  



End file.
